Skip to main content

Advertisement

Log in

Self-assembled polymer vesicles in deciding action of Zn-sulfanilamide allergenicity

  • Research Article
  • Published:
Drug Delivery and Translational Research Aims and scope Submit manuscript

Abstract

Allergic reactions to sulfonamide-based drugs are quite common; hence, medications containing sulfonamides are prescribed carefully. Metal ion complexation may block the nitrogen binding site of sulfonamide by complexation and reduce such responses. In this study, trace concentrations of Zn were found to bind with sulfanilamide at pH ∼ 1. The complexation was studied in water as well as in vesicular medium of polyethylene glycol (PEG) and a block copolymer, PPG-PEG-PPG. The binding constants (k) of Zn-sulfanilamide complex were determined in water, PEG, and PPG-PEG-PPG block copolymer media. The values suggest that complexation occurs best in water followed by PPG-PEG-PPG, PEG #4000, and PEG #12000. Though the binding constants are high in water and block copolymer media, the complex is not very stable as the absorbance value for the complex was found to decline with time. The same complex when prepared in polymer matrix shows higher stability. The results prompted us to explore the extraction possibilities of the Zn-sulfanilamide complex by using aqueous biphasic extraction systems comprising the polymers against sodium sulfate solution. The complex was analyzed for its allergenic response in different media by competitive enzyme-linked immunosorbent assay (ELISA) technique. The allergic response of the compounds in the respective media is the resultant of the binding constant and the stability of the complex in that particular medium.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Zhang CL, Wang FA, Wang Y. Solubilities of sulfadiazine, sulfamethazine, sulfadimethoxine, sulfamethoxydiazine, sulfamonomethoxine, sulfamethoxazole, and sulfachloropyrazine in water from (298.15 to 333.15) K. J Chem Eng Data. 2007;52:1563–6.

    Article  CAS  Google Scholar 

  2. Martinez F, Gomez A. Thermodynamic study of the solubility of some sulfonamides in cyclohexane. J Solution Chem. 2001;30:909–22.

    Article  CAS  Google Scholar 

  3. Delgado JN, Remers WA. Wilson and Gisvold text book of organic medicinal and pharmaceutical chemistry. 9th ed. New York: Lippincott; 1991.

    Google Scholar 

  4. Chaudhary PR, Sen DJ. Complexation: effect of metal on microbiological activity of sulfanilamide derivatives. Am J Adv Drug Deliv. 2013;1:149–56.

    Google Scholar 

  5. Blasco F, Perelló L, Latorre J, Borrás JS, Garciá-Granda. Cobalt(II), nickel(II), and copper(II) complexes of sulfanilamide derivatives: synthesis, spectroscopic studies, and antibacterial activity. Crystal structure of [Co(sulfacetamide)2(NCS)2]. J Inorg Biochem. 1996;61:143–54.

    Article  CAS  PubMed  Google Scholar 

  6. Ferrer S, Borrás J, Garcia-España E. Complex formation equilibria between the acetazolamide ((5-acetamido-1,3,4-thiadiazole)-2-sulphonamide), a potent inhibitor of carbonicanhydrase, and Zn(II), Co(II), Ni(II) and Cu(II) in aqueous and ethanol-aqueous solutions. J Inorg Biochem. 1990;39:297–306.

    Article  CAS  Google Scholar 

  7. Supuran CT, Mincione F, Scozzafava A, Briganti F, Mincinone GM, Ilies MA. Carbonic anhydrase inhibitors—part 52. Metal complexes of heterocyclic sulfonamides: a new class of strong topical intraocular pressure-lowering agents in rabbits. Eur J Med Chem. 1998;33:247–334.

    Article  CAS  Google Scholar 

  8. Supuran CT, Scozzafava A. Novel aromatic heterocyclic sulfonamides and their metal-complexes as inhibitors of carbonic-anhydrase isozyme-I, isozyme-II and isozyme-IV. JEnzyme Inhib. 1997;13:37–51.

    Article  Google Scholar 

  9. Jitianu A, Ilies MA, Scozzafava AC, Supuran T. Complexes with biologically active ligands-part 8. Synthesis and carbonic anhydrase inhibitory activity of 5-benzoyl amido and 5,3-(nitro benzoyl amido) 1,3, −thiadiazole 2-sulphonamide and their metal complexes. Main Group Met Chem. 1997;20:151–6.

    Article  CAS  Google Scholar 

  10. Scozzafava A, Menabuoni L, Mincione F, Briganti F, Mincinone G, Supuran CT. J Med Chem. 1999;42:2641–50.

    Article  CAS  PubMed  Google Scholar 

  11. Casanova J, Alzuet G, Ferrer S, Borrás J, García-Granda S, Perez-Carreño E. Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring? J Inorg Biochem. 1993;51:689–761.

    Article  CAS  Google Scholar 

  12. Casanova J, Alzuet G, Borrás J, David L, Gatteschi D. Metal complexes of sulfanilamide derivatives. Spectroscopic characterization of the dichloro disulfathiazole methanol copper(II) complex. Inorg Chim Acta. 1993;211:183–6.

    Article  CAS  Google Scholar 

  13. García-Raso A, Fiol JJ, Martorell G, López-Zafra A, Quirós M. Metallation of 2-sulfanilamidopyrimidine (sulfadiazine). X-ray diffraction structure and solution behaviour of bis(sulfadiazinato) mercury(II) bis(dimethylsulfoxide). Polyhedron. 1997;16:613–21.

    Article  Google Scholar 

  14. Kucera CM, Greenberger PA. Adverse drug reactions: treatment and prevention. Hosp Med. 1996;32:11–24.

    Google Scholar 

  15. Bond CA. Skin disorders I. Applied therapeutics: the clinical use of drugs. Koda Kimble MA, Young L (eds). Vancouver, Applied Therapeutics, 5th Ed, p 64–18, 1991.

  16. Vassileva S. Drug-induced pemphigoid: bullous and cicatricial. Clin Dermatol. 1998;16:379–87.

    Article  CAS  PubMed  Google Scholar 

  17. Dunca RN, Vicent MJ. Polymer therapeutics-prospects for 21st century: the end of the beginning. Adv Drug Deliv Rev. 2013;65:60–70.

    Article  Google Scholar 

  18. Torchilin VP. Targeted polymeric micelles for delivery of poorly soluble drugs. Cell Mol Life Sci. 2004;61:2549–59.

    Article  CAS  PubMed  Google Scholar 

  19. Kopeek J, Kopekova P. HPMA copolymers: origins, early developments, present, and future. Adv Drug Deliv Rev. 2010;62:122–49.

    Article  Google Scholar 

  20. Xu Y, de Souza MA, Ribeiro-Pontes MZ, Vitolo M, Pessoa-Jr A. Liquid-liquid extraction of pharmaceuticals by aqueous two-phase Systems. Br J Pharm Sci. 2001;37:2015–22.

    Google Scholar 

  21. Wei DZ, Zhu JH, Cao XJ. Enzymatic synthesis of cephalexin in aqueous two-phase systems. Biochem Eng J. 2002;11:95–9.

    Article  CAS  Google Scholar 

  22. Ghatak SK, Dey D, Sen S, Sen K. Aromatic amino acids in high selectivity bismuth (III) recognition. Analyst. 2013;138:2308–14.

    Article  CAS  PubMed  Google Scholar 

  23. Pearson RG. Hard and soft acids and bases. J Am Chem Soc. 1963;85:3533–9.

    Article  CAS  Google Scholar 

  24. Paik SP, Ghatak SK, Dey D, Sen K. Polyethylene glycol vesicles: self assembled site for luminescence generation. Anal Chem. 2012;84:7555–61.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the University Grants Commission (UGC, Sanction No. 41-248/2012 (SR)) for funding. One of the authors, S. P. P., acknowledges the University Grants Commission (N. PSW-47/12-13, dt 05.02.2013, S No. 213956) for funding. P. S. expresses sincere thanks to the UGC, India [Memo No. UGC/1228C/Major Research (SC) 2012] for providing the necessary fellowship.

Conflict of interest

There is no conflict of interest regarding the article. No animal studies were performed.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kamalika Sen.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Paik, S.P., Samaddar, P., Sen, S. et al. Self-assembled polymer vesicles in deciding action of Zn-sulfanilamide allergenicity. Drug Deliv. and Transl. Res. 4, 409–415 (2014). https://doi.org/10.1007/s13346-014-0203-1

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13346-014-0203-1

Keywords

Navigation